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Portland

$160+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Aug 6 — Aug 131
Thu 8/6
Thu 8/13
1 adult, Economy
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Find cheap flights from O'Hare Intl to Portland with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in March or May, booked 85 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap flight deals from O'Hare Intl to Portland

Cheapest flights from O'Hare Intl to Portland
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 7, 2026.

This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:05 am
ORD
-
PWM
Nonstop2h 33m
American Airlines
Sat 9/54:07 pm
PWM
-
ORD
Nonstop3h 07m
American Airlines
Deal found 7/7$298
This CheapOair deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
ORD
-
PWM
1 stop6h 45m
JetBlue
Sun 8/306:00 am
PWM
-
ORD
1 stop27h 43m
JetBlue
Deal found 7/7$301
This CheapOair deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:30 am
ORD
-
PWM
1 stop16h 22m
JetBlue
Tue 10/66:00 am
PWM
-
ORD
1 stop6h 47m
JetBlue
Deal found 7/7$302
This lol.travel deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:27 pm
ORD
-
PWM
1 stop5h 58m
JetBlue
Mon 8/106:00 am
PWM
-
ORD
1 stop27h 43m
JetBlue
Deal found 7/5$305
This American Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:13 pm
ORD
-
PWM
Nonstop2h 35m
American Airlines
Tue 8/2512:09 pm
PWM
-
ORD
Nonstop3h 00m
American Airlines
Deal found 7/4$306
This American Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:05 am
ORD
-
PWM
Nonstop2h 33m
American Airlines
Tue 8/2512:09 pm
PWM
-
ORD
Nonstop3h 00m
American Airlines
Deal found 7/6$307
This JetBlue deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
ORD
-
PWM
1 stop5h 17m
JetBlue
Fri 8/72:45 pm
PWM
-
ORD
1 stop8h 13m
JetBlue
Deal found 7/6$308
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:05 am
ORD
-
PWM
Nonstop2h 33m
American Airlines
Wed 8/269:08 am
PWM
-
ORD
Nonstop2h 59m
American Airlines
Deal found 7/5$309
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:13 pm
ORD
-
PWM
Nonstop2h 35m
American Airlines
Mon 8/246:09 pm
PWM
-
ORD
Nonstop3h 21m
American Airlines
Deal found 7/3$310
This CheapOair deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
ORD
-
PWM
1 stop6h 54m
JetBlue
Sat 8/86:41 am
PWM
-
ORD
1 stop16h 17m
JetBlue
Deal found 7/2$311
This Priceline deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:00 pm
ORD
-
PWM
1 stop9h 52m
JetBlue
Mon 9/286:00 am
PWM
-
ORD
1 stop6h 47m
JetBlue
Deal found 7/7$312
This CheapOair deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:27 pm
ORD
-
PWM
1 stop5h 58m
JetBlue
Sat 8/156:41 am
PWM
-
ORD
1 stop16h 17m
JetBlue
Deal found 7/6$313

Find flight deals from O'Hare Intl to Portland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$301
(CheapOair)

One-way from

$160
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$393

Good round-trip deal

$362 or less

Good one-way deal

$215 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Portland flights.
Search Deals
From Chicago O'Hare Intl to Portland
Search Deals
One-way flight from Chicago O'Hare Intl to Portland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 7, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/8

6:08 pm-9:41 pm

Nonstop2h 33m

Portland

Tue 8/11

6:00 am-7:57 am

Nonstop2h 57m

$307

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 8/19

10:33 am-11:30 pm

2 stops11h 57m

Portland

Wed 8/26

6:00 am-12:17 pm

1 stop7h 17m

$332

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 9/6

5:30 am-2:23 pm

2 stops7h 53m

Portland

Thu 9/10

1:59 pm-11:59 pm

2 stops11h 00m

$363

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 7/29

6:00 am-1:45 pm

1 stop6h 45m

Portland

Thu 8/6

2:40 pm-9:58 pm

1 stop8h 18m

$371

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 10/1

6:59 am-10:40 am

Nonstop2h 41m

Portland

Mon 10/5

5:08 pm-7:05 pm

Nonstop2h 57m

$401

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 10/4

1:55 pm-11:30 pm

2 stops8h 35m

Portland

Sun 10/11

6:28 am-10:30 am

1 stop5h 02m

$426

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 7/31

6:08 pm-9:41 pm

Nonstop2h 33m

Portland

Sun 8/2

6:00 am-8:00 am

Nonstop3h 00m

$442

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 7/31

9:30 pm-11:30 pm

1 stop25h 00m

Portland

Tue 8/4

5:15 am-11:29 am

2 stops7h 14m

$456

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 7/22

6:08 pm-9:41 pm

Nonstop2h 33m

Portland

Sun 7/26

6:00 am-8:00 am

Nonstop3h 00m

$457

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 8/6

6:08 pm-9:41 pm

Nonstop2h 33m

Portland

Sun 8/9

6:00 am-8:00 am

Nonstop3h 00m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from O'Hare Intl to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Portland in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Portland

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 80 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Currently, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $300). Flying from Chicago O'Hare Intl Airport to Portland, Maine in December is currently the most expensive (average of $441). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to PWM?

Find hourly flight availability from O'Hare Intl to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 7, 2026.

When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 22% versus a flight in the afternoon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on July 4, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Portland, Maine?

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated July 7, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,944 reviews

Entertainment

7.1

Food

6.7

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
United Airlines
7.4
Good
9,944 reviews
United Airlines
7.4
Good
9,944 reviews

Entertainment

7.1

Food

6.7

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.
American Airlines
7.1
Good
11,782 reviews
United Airlines
7.4
Good
9,944 reviews

Entertainment

7.1

Food

6.7

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Tim,May 2023

ORD - DLH

Didn’t have to wait long for the plane and was in the lounge through that time could relax there made it nice.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 7 inbound flights from Chicago O'Hare Intl per day. 2 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • How long is the flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Departing from Chicago O'Hare Intl Airport to Portland, Maine will take you 2h 33m. There are 897 mi between Chicago O'Hare Intl Airport and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Portland, Maine round-trip?

    According to our current data, American Airlines ($229), and United Airlines ($229) offers the cheapest pricing from Chicago O'Hare Intl Airport to Portland, Maine. You may be able to fly from Chicago O'Hare Intl Airport to Portland, Maine for 37% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Portland, Maine?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Portland, Maine are SkyWest Airlines (93%), Envoy Air (82%) and American Airlines (82%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Portland, Maine?

    While on average a flight from Chicago O'Hare Intl Airport to Portland, Maine is generally $336, our data shows the cheapest flight currently is $158. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $185 for that flight.

  • Can I find deals for flights from O'Hare Intl to Portland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Portland.

  • Can I find deals for business class flights from O'Hare Intl to Portland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Currently, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $300). Flying from Chicago O'Hare Intl Airport to Portland, Maine in December is currently the most expensive (average of $441). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Lewiston
Brunswick
Conway

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Alternative routes for O'Hare Intl to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights
Midway to Boston flights
O'Hare Intl to Bangor flights
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O'Hare Intl to Bar Harbor flights

Top 2 airlines flying from O'Hare Intl to Portland

Discover the top 2 airlines that operate flights from O'Hare Intl to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$229Average$363FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$371FlexibilityNo cancel feeOn-time69%

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